Originally Posted by sneuman
Well, it's your tripů
I somehow thought you were leaving from the Bahamas
, so had the Windward Passage
in mind, but now I reread it and see you are leaving from the Keys, which changes things a little bit.
If you decide to do North Cuba
, then you are probably best to drop South through the Caymans from there and things will be a little bit tighter to the wind
than if you were coming more from the East.
Or preferably you could go around to the South coast of Cuba
and make your way more East in the protection of the land and drop south with the wind
at a greater angle.
It doesn't make a lot of sense to go through the Windward Passage from the Keys.
But if you go the E Caribe route
, you will be needing to make 3,000 miles in 4 months, with half of them upwind and the other half in strong winds/waves. The Western/Central passage will be less than half that distance in more favorable conditions.